US6028215A - Process for preparing esters of carboxylic acids - Google Patents

Process for preparing esters of carboxylic acids Download PDF

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Publication number
US6028215A
US6028215A US09/109,767 US10976798A US6028215A US 6028215 A US6028215 A US 6028215A US 10976798 A US10976798 A US 10976798A US 6028215 A US6028215 A US 6028215A
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United States
Prior art keywords
alcohol
internals
carboxylic acid
column
reactive
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Expired - Lifetime
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US09/109,767
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English (en)
Inventor
Bernd Bessling
Bernd Lohe
Rudiger Welker
Walter Disteldorf
Jean Werner Knab
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BASF SE
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BASF SE
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Assigned to BASF AKTIENGESELLSCHAFT reassignment BASF AKTIENGESELLSCHAFT ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BESSLING, BERND, DISTELDORF, WALTER, LOHE, BERND, WELKER, RUEDIGER, WERNER, JEAN
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/009—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping in combination with chemical reactions
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01D—SEPARATION
    • B01D3/00—Distillation or related exchange processes in which liquids are contacted with gaseous media, e.g. stripping
    • B01D3/14—Fractional distillation or use of a fractionation or rectification column
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/32—Packing elements in the form of grids or built-up elements for forming a unit or module inside the apparatus for mass or heat transfer
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
    • B01J8/02—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds
    • B01J8/04—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds the fluid passing successively through two or more beds
    • B01J8/0446—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds the fluid passing successively through two or more beds the flow within the beds being predominantly vertical
    • B01J8/0449—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds the fluid passing successively through two or more beds the flow within the beds being predominantly vertical in two or more cylindrical beds
    • B01J8/0453—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes with stationary particles, e.g. in fixed beds the fluid passing successively through two or more beds the flow within the beds being predominantly vertical in two or more cylindrical beds the beds being superimposed one above the other
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/48—Separation; Purification; Stabilisation; Use of additives
    • C07C67/52—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
    • C07C67/54—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2208/00—Processes carried out in the presence of solid particles; Reactors therefor
    • B01J2208/00796—Details of the reactor or of the particulate material
    • B01J2208/00805—Details of the particulate material
    • B01J2208/00814—Details of the particulate material the particulate material being provides in prefilled containers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/10—Process efficiency

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • Thermal Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Physical Or Chemical Processes And Apparatus (AREA)
US09/109,767 1997-07-04 1998-07-06 Process for preparing esters of carboxylic acids Expired - Lifetime US6028215A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19728683 1997-07-04
DE19728683 1997-07-04

Publications (1)

Publication Number Publication Date
US6028215A true US6028215A (en) 2000-02-22

Family

ID=7834698

Family Applications (1)

Application Number Title Priority Date Filing Date
US09/109,767 Expired - Lifetime US6028215A (en) 1997-07-04 1998-07-06 Process for preparing esters of carboxylic acids

Country Status (7)

Country Link
US (1) US6028215A (ja)
JP (1) JP4390298B2 (ja)
CN (1) CN1130329C (ja)
BE (1) BE1014031A3 (ja)
DE (1) DE19829809B4 (ja)
ES (1) ES2153291B1 (ja)
MY (1) MY124268A (ja)

Cited By (26)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6458992B1 (en) * 1998-03-25 2002-10-01 Sulzer Chemtech Ag Process and apparatus for the production of butylacetate and isobutylacetate
US20030018224A1 (en) * 2000-02-04 2003-01-23 Yasuo Tsuji High-purity 1,3-butylen glycol, process for producing 1,3-butylene glycol, and process for producing by -product butanol and butyl acetate
WO2003040268A1 (de) * 2001-11-09 2003-05-15 GMK-Gesellschaft für Motoren und Kraftanlagen mbH Verfahren zur herstellung von kraftstoffen aus sauren fetten und anlage zu dessen durchführung
US6573400B1 (en) 1999-08-19 2003-06-03 Basf Aktiengesellschaft Preparation of 2-keto-L-gulonic esters
US6693213B1 (en) 1999-10-14 2004-02-17 Sulzer Chemtech Ag Method of producing ethyl acetate and an equipment for carrying out this method
US20050096481A1 (en) * 2001-10-05 2005-05-05 Rainer Hildebrandt Method for producing a hydroxyacid esters
US20060041162A1 (en) * 2004-08-18 2006-02-23 Warner R J Acetic anhydride and acetate ester co-production
US20060058550A1 (en) * 2002-11-11 2006-03-16 Basf Aktiengesellschaft Method for the production of 2 =-keto-l-gulonic acid c4-c10 alkyl esters
US20060178524A1 (en) * 2005-02-10 2006-08-10 Laurent Zuber Method and plant for the manufacture of carboxylic acid ester by means of a reactive distillation
US20070203358A1 (en) * 2006-02-28 2007-08-30 Hendrik Dirkzwager Process for reactive distillation of a carboxylic acid
US20080264772A1 (en) * 2007-04-25 2008-10-30 National Taiwan University Method and apparatus for esterification
US20090137825A1 (en) * 2006-04-04 2009-05-28 Christophe Bauduin Method of producing a carboxylic alkyl ester
US20100249457A1 (en) * 2009-03-24 2010-09-30 Ji-Young Jang Apparatus and method for recovery of acetic acid from an aqueous solution thereof
WO2011023662A1 (fr) 2009-08-24 2011-03-03 Rhodia Operations Procede d'esterification d'acide carboxylique
US20110076207A1 (en) * 2009-09-29 2011-03-31 Lanxess Sybron Chemicals Inc. Method and apparatus for protecting and monitoring the kinetic performance of an esterification catalyst material
WO2012164573A2 (en) 2011-05-27 2012-12-06 Reliance Industries Ltd., Hydrolysis and esterification with acid catalysts
US8785697B2 (en) 2011-06-24 2014-07-22 Eastman Chemical Company Nickel modified catalyst for the production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US8829206B2 (en) 2011-06-24 2014-09-09 Eastman Chemical Company Production of cyclic acetals or ketals using solid acid catalysts
US8829207B2 (en) 2011-06-24 2014-09-09 Eastman Chemical Company Production of cyclic acetals by reactive distillation
US8969598B2 (en) 2011-06-24 2015-03-03 Eastman Chemical Company Production of cyclic acetals or ketals using liquid-phase acid catalysts
US9000229B2 (en) 2011-06-24 2015-04-07 Eastman Chemical Company Production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US9056313B2 (en) 2011-06-24 2015-06-16 Eastman Chemical Company Catalysts for the production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US9328054B1 (en) 2013-09-27 2016-05-03 Travis Danner Method of alcoholisis of fatty acids and fatty acid gyicerides
US9388105B2 (en) 2011-06-24 2016-07-12 Eastman Chemical Company Production of hydroxy ether hydrocarbons by liquid phase hydrogenolysis of cyclic acetals or cyclic ketals
CN116272675A (zh) * 2023-02-20 2023-06-23 安徽瑞柏新材料有限公司 基于催化蒸馏法的乙酸丙酯制备装置
CN116271906A (zh) * 2023-03-14 2023-06-23 安徽瑞柏新材料有限公司 一种环保低能耗连续式乙酸丁酯制备设备

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1424115B1 (de) * 2002-11-28 2016-01-13 Sulzer Chemtech AG Verfahren zum Verestern einer Fettsäure
TWI324592B (en) 2002-11-28 2010-05-11 Sulzer Chemtech Ag A method for the esterification of a fatty acid
EP1690849B1 (de) * 2005-02-10 2009-08-26 Sulzer Chemtech AG Verfahren zur Herstellung von Carbonsäureester mittels einer Reaktivdestillation
CN100395226C (zh) * 2006-03-20 2008-06-18 无锡百川化工股份有限公司 以硫酸为催化剂反应精馏法规模化生产乙酸丁酯的方法
JP4593638B2 (ja) * 2008-02-18 2010-12-08 ダイセル化学工業株式会社 エステル系溶剤の製造方法
CN101519349B (zh) * 2008-02-27 2015-02-25 中国石油化学工业开发股份有限公司 利用酸和醇制造酯类的方法和系统
CN101781200B (zh) * 2009-01-20 2013-04-03 中国石油化学工业开发股份有限公司 有机羧酸酯的制造方法
CN101948384B (zh) * 2010-10-14 2013-11-06 谢仁华 连续式酯化法制备中高碳脂肪酸酯的设备和方法
CN102249913B (zh) * 2011-05-17 2013-11-06 上海华谊丙烯酸有限公司 一种制备丙烯酸丁酯的方法
JP2015030700A (ja) * 2013-08-02 2015-02-16 株式会社ダイセル エステル系溶剤の製造方法
KR102019037B1 (ko) * 2017-05-26 2019-09-06 지에스칼텍스 주식회사 알킬 카르복실산 에스테르의 제조 방법

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4314947A (en) * 1978-12-21 1982-02-09 Basf Aktiengesellschaft Process for completing the esterification of carboxylic acids with alcohols
US4939294A (en) * 1989-05-22 1990-07-03 Eastman Kodak Company Preparation of ultra high purity methyl acetate
US5008046A (en) * 1988-03-21 1991-04-16 Henkel Kommanditgesellschaft Auf Aktien Process for the continuous esterification of fatty acids

Family Cites Families (5)

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Publication number Priority date Publication date Assignee Title
DE1768104C3 (de) * 1968-04-01 1974-07-18 Wacker-Chemie Gmbh, 8000 Muenchen Verfahren zur kontinuierlichen Herstellung von praktisch carbonsäurefreien Estern aus wasserunlöslichen C tief 4 -C tief 6 -Alkoholen und gesättigten aliphatischen Carbonsäuren mit 2- 4 C-Atomen
DE2756748A1 (de) * 1977-12-20 1979-06-28 Basf Ag Verfahren zur vervollstaendigung der veresterung von carbonsaeuren mit alkoholen
DE3121383C2 (de) * 1981-05-29 1983-04-14 Chemische Werke Hüls AG, 4370 Marl Verfahren zur Veresterung von Essigsäure mit C↓2↓- bis C↓5↓-Alkoholen
DE69027304T2 (de) * 1989-01-17 1997-01-23 Davy Process Technology Ltd., London Kontinuierliches Verfahren zur Herstellung von Carbonsäureestern
DE69313068T2 (de) * 1992-10-22 1998-03-05 Sumitomo Chemical Co Verfahren zur Herstellung von Methylmethacrylat

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4314947A (en) * 1978-12-21 1982-02-09 Basf Aktiengesellschaft Process for completing the esterification of carboxylic acids with alcohols
US5008046A (en) * 1988-03-21 1991-04-16 Henkel Kommanditgesellschaft Auf Aktien Process for the continuous esterification of fatty acids
US4939294A (en) * 1989-05-22 1990-07-03 Eastman Kodak Company Preparation of ultra high purity methyl acetate

Cited By (46)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7160524B2 (en) 1998-03-25 2007-01-09 Sulzer Chemtech Ag Process and apparatus for the production of butylacetate and isobutylacetate
US20020183545A1 (en) * 1998-03-25 2002-12-05 Sulzer Chemtech Ag Process and apparatus for the production of butylacetate and isobutylacetate
US6458992B1 (en) * 1998-03-25 2002-10-01 Sulzer Chemtech Ag Process and apparatus for the production of butylacetate and isobutylacetate
US6573400B1 (en) 1999-08-19 2003-06-03 Basf Aktiengesellschaft Preparation of 2-keto-L-gulonic esters
US6693213B1 (en) 1999-10-14 2004-02-17 Sulzer Chemtech Ag Method of producing ethyl acetate and an equipment for carrying out this method
US20030018224A1 (en) * 2000-02-04 2003-01-23 Yasuo Tsuji High-purity 1,3-butylen glycol, process for producing 1,3-butylene glycol, and process for producing by -product butanol and butyl acetate
US6900360B2 (en) 2000-02-04 2005-05-31 Daicel Chemical Industries, Ltd. High-purity 1,3-butylen glycol, process for producing 1,3-butylene glycol, and process for producing by-product butanol and butyl acetate
US20050096481A1 (en) * 2001-10-05 2005-05-05 Rainer Hildebrandt Method for producing a hydroxyacid esters
CN1305833C (zh) * 2001-10-05 2007-03-21 海尔特曼公司 羟基酸酯的制备方法
WO2003040268A1 (de) * 2001-11-09 2003-05-15 GMK-Gesellschaft für Motoren und Kraftanlagen mbH Verfahren zur herstellung von kraftstoffen aus sauren fetten und anlage zu dessen durchführung
US20040186307A1 (en) * 2001-11-09 2004-09-23 Gmk-Gesellschaft Fur Motoren Method for the production of fuel from acid fats and system for carrying out said method
US7456305B2 (en) 2001-11-09 2008-11-25 Gmk-Gesellschaft Fur Motoren Und Kraftanlagen Mbh Method for the production of fuel from acid fats and system for carrying out said method
US7091375B2 (en) 2002-11-11 2006-08-15 Basf Aktiengesellschaft Method for the production of 2=-keto-l-gulonic acid C4C10 alkyl esters
US20060058550A1 (en) * 2002-11-11 2006-03-16 Basf Aktiengesellschaft Method for the production of 2 =-keto-l-gulonic acid c4-c10 alkyl esters
US7199263B2 (en) 2004-08-18 2007-04-03 Celanese International Corporation Acetic anhydride and acetate ester co-production
US20060041162A1 (en) * 2004-08-18 2006-02-23 Warner R J Acetic anhydride and acetate ester co-production
US20060178524A1 (en) * 2005-02-10 2006-08-10 Laurent Zuber Method and plant for the manufacture of carboxylic acid ester by means of a reactive distillation
US7329774B2 (en) * 2005-02-10 2008-02-12 Sulzer Chemtech Ag Method and plant for the manufacture of carboxylic acid ester by means of a reactive distillation
US20070203358A1 (en) * 2006-02-28 2007-08-30 Hendrik Dirkzwager Process for reactive distillation of a carboxylic acid
US7718039B2 (en) 2006-02-28 2010-05-18 Shell Oil Company Process for reactive distillation of a carboxylic acid
US8410306B2 (en) 2006-04-04 2013-04-02 Basf Se Method of producing a carboxylic alkyl ester
US20090137825A1 (en) * 2006-04-04 2009-05-28 Christophe Bauduin Method of producing a carboxylic alkyl ester
US20080264772A1 (en) * 2007-04-25 2008-10-30 National Taiwan University Method and apparatus for esterification
US7857944B2 (en) * 2007-04-25 2010-12-28 National Taiwan University Method and apparatus for esterification
US20100249457A1 (en) * 2009-03-24 2010-09-30 Ji-Young Jang Apparatus and method for recovery of acetic acid from an aqueous solution thereof
US8268131B2 (en) * 2009-03-24 2012-09-18 Amt International, Inc. Apparatus and method for recovery of acetic acid from an aqueous solution thereof
US8506766B2 (en) * 2009-03-24 2013-08-13 Amt International Inc. Method for recovery of acetic acid from an aqueous solution thereof
WO2011023662A1 (fr) 2009-08-24 2011-03-03 Rhodia Operations Procede d'esterification d'acide carboxylique
US20110076207A1 (en) * 2009-09-29 2011-03-31 Lanxess Sybron Chemicals Inc. Method and apparatus for protecting and monitoring the kinetic performance of an esterification catalyst material
WO2012164573A2 (en) 2011-05-27 2012-12-06 Reliance Industries Ltd., Hydrolysis and esterification with acid catalysts
US9056313B2 (en) 2011-06-24 2015-06-16 Eastman Chemical Company Catalysts for the production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US9394271B2 (en) 2011-06-24 2016-07-19 Eastman Chemical Company Production of cyclic acetals or ketals using liquid-phase acid catalysts
US8829207B2 (en) 2011-06-24 2014-09-09 Eastman Chemical Company Production of cyclic acetals by reactive distillation
US8969598B2 (en) 2011-06-24 2015-03-03 Eastman Chemical Company Production of cyclic acetals or ketals using liquid-phase acid catalysts
US9000229B2 (en) 2011-06-24 2015-04-07 Eastman Chemical Company Production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US8785697B2 (en) 2011-06-24 2014-07-22 Eastman Chemical Company Nickel modified catalyst for the production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US9315485B2 (en) 2011-06-24 2016-04-19 Eastman Chemical Company Production of cyclic acetals by reactive distillation
US9440944B2 (en) 2011-06-24 2016-09-13 Eastman Chemical Company Production of cyclic acetals or ketals using solid acid catalysts
US9382179B2 (en) 2011-06-24 2016-07-05 Eastman Chemical Company Nickel modified catalyst for the production of hydroxy ether hydrocarbons by vapor phase hydrogenolysis of cyclic acetals and ketals
US9388105B2 (en) 2011-06-24 2016-07-12 Eastman Chemical Company Production of hydroxy ether hydrocarbons by liquid phase hydrogenolysis of cyclic acetals or cyclic ketals
US8829206B2 (en) 2011-06-24 2014-09-09 Eastman Chemical Company Production of cyclic acetals or ketals using solid acid catalysts
US9328054B1 (en) 2013-09-27 2016-05-03 Travis Danner Method of alcoholisis of fatty acids and fatty acid gyicerides
CN116272675A (zh) * 2023-02-20 2023-06-23 安徽瑞柏新材料有限公司 基于催化蒸馏法的乙酸丙酯制备装置
CN116272675B (zh) * 2023-02-20 2023-10-17 安徽瑞柏新材料有限公司 基于催化蒸馏法的乙酸丙酯制备装置
CN116271906A (zh) * 2023-03-14 2023-06-23 安徽瑞柏新材料有限公司 一种环保低能耗连续式乙酸丁酯制备设备
CN116271906B (zh) * 2023-03-14 2023-09-22 安徽瑞柏新材料有限公司 一种环保低能耗连续式乙酸丁酯制备设备

Also Published As

Publication number Publication date
MY124268A (en) 2006-06-30
CN1204640A (zh) 1999-01-13
JP4390298B2 (ja) 2009-12-24
DE19829809B4 (de) 2015-09-10
BE1014031A3 (fr) 2003-03-04
JPH1192417A (ja) 1999-04-06
ES2153291B1 (es) 2001-07-01
ES2153291A1 (es) 2001-02-16
CN1130329C (zh) 2003-12-10
DE19829809A1 (de) 1999-01-07

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